Crystal and Molecular Structures of Three Organic Salts from Nevirapine

Abstract

The preparation, X-ray crystal structure, Fourier Transform infrared (FTIR) spectroscopy, and elemental analysis of three compounds of the non-nucleoside reverse transcriptase inhibitor nevirapine are reported. XRD and FTIR analysis indicated that all these complexes are organic salt. The compound 1 crystallizes in the triclinic, space group P-1, with a = 9.147(1) Å , b = 9.494(2) Å , c = 11.948(2) Å , a = 111.079 (2)°, b = 90.0890(10)°, c = 95.0780(10)°,V = 963.7(3) Å 3 , Z = 2. The compound 2 crystallizes in the monoclinic, space group C2/c, with a = 21.608(2) Å , b = 12.860(1) Å , c = 15.653(1) Å , b = 92.2940(10)°, V = 4346.1(6) Å 3 , Z = 8. The compound 3 crystallizes in the monoclinic, space group P2(1)/c, with a = 9.013(1) Å , b = 26.580(2) Å , c = 8.360(1) Å , b = 114.789(2)°, V = 1818.3(3) Å 3 , Z = 4. Nevirapine molecules are linked essentially by the N-HÁÁÁO hydrogen bonds, forming centrosymmetric dimers.In the dimers every nevirapine displays a butterflylike conformation with the cyclopropyl group directed towards the concave face of the molecule. In this work, the hydrogen bonding interactions in the salts have been investigated. The role of weak and strong hydrogen bonding in the crystal packing is ascertained. Graphical Abstract In the three prepared salts there are plenty of weak nonbonding interactions such as directional hydrogen bonds of N-HÁÁÁO (neutral and ionic), intra-and interchain CH-N, CH n ÁÁÁO (n = 1, 2, 3), CH-S, O-C contact, O-p, CH n -p (n = 1 and 2), and p-p interactions. Due to these collective weak interactions, all the compounds displayed 3D framework structures.

Optimization and comparison of statistical tools for the prediction of multicomponent forms of a molecule: the antiretroviral nevirapine as a case study

“…There are several multicomponent forms containing NVP that are reported in the literature. Performing a search on the CSD database, nine solvates, [28][29][30][31][32] eight co-crystals, 20,21,33 and four salts 34,35 containing the NVP molecule were found, besides the anhydrous 26,32 and hemihydrate forms 31,32 (Fig. 3).…”

Syntheses, Crystal Structures, and Thermal Properties of Energetic Semicarbazide Salt, Manganese(II) Salt, and Coordination Compound of 3,5‐Dinitrobenzoic Acid

“…Aromatic carboxyl acid as a multifunctional ligand has recently aroused considerable interest in the design and synthesis of functional coordination compounds . 3,5‐Dinitrobenzoic acid (HDNBA) is the 3,5‐nitro superseded benzoic acid, which has aroused the most interest on organic supramolecular architecture and metallorganics because of its potential applications for catalyst, optical and magnetic materials. However, reports on DNBA based compounds as energetic materials are rare.…”